The loss of the 2004 Belmont Stakes (gr. I) by Smarty Jones still plays in Stewart Elliott’s mind, especially around this time of year. He thinks of the pressure going into that race, remembering the media frenzy and build-up of public recognition. He recalls his trip, how race-riding tactics and his mount’s reluctance to settle eventually cost him the score. If the horse had run back to his Kentucky Derby (gr. I) and Preakness (gr. I)-winning form, he believes they could have won the Triple Crown.

Elliott, 43, was the most recent rider to pursue this elusive trophy. Before him, 28 jockeys attempted to claim a Triple Crown as their own. He was the 17th to have failed, one of four who are still riding to this day. Kent Desormeaux, who will bid for the Triple Crown for trainer Rick Dutrow Jr. aboard IEAH Stables' Big Brown in the June 7 Belmont, Victor Espinosa, and Patrick Valenzuela make up the distinguished quartet.

“This time of year brings it back and makes you think about it,” said Elliott, who rode the John Servis-trained Smarty Jones for Roy Chapman’s Someday Farm. “I think the horse would have won if he’d run like he’d run before, like he ran in the Derby or Preakness. But that day, that particular day, it wasn’t meant to be.”

The path that brings a rider to Belmont Park aboard a Triple Crown contender is a glorious one, paved by Classic scores that are satisfying on their own. But the pursuit of greatness continues in the Belmont, and the loss of such a quest is one these riders never forget.

Jose Santos, 47, counts the loss of Funny Cide in the 2003 Belmont as a disappointment, but one for which he does not feel responsible. Aboard the Sackatoga Stables-owned and Barclay Tagg-trained gelding, the now-retired Hall of Fame jockey coasted in third. He considered the effort a strong one from his mount, and was pleased with the results. Still, that didn’t ease the sting of defeat.

“It’s very simple,” he said. “Jockeys are only going to spend 2 ½ minutes racing on top of the horse. When you win the Derby and Preakness you feel like a cinch to be the next Triple Crown winner, but after the Preakness a lot of times that can’t happen. Horses are very delicate and a lot of things happen between the races; all the responsibility for those three weeks is on the trainer and the people who take care of the horse. But people criticize the jockey who doesn’t win the race, because you’re supposed to win the race.”

Apart from the time between efforts, another factor often hampers a rider’s shot at the Triple Crown; by the Belmont, his contenders know the weaknesses of his mount. They are gunning for him from the start, chasing as if a solid bull’s eye has been painted on his back. Race-riding techniques, while fair, can be brutal to a jockey’s game.

“We started off with a sprinter,” Elliott remembered. “He was very fast, and we said ‘If we can get this horse throttle down the speed and get him to stretch out, we’ll really have something here.’ He could have done it, but that day he wouldn’t relax because he had a horse up beside him from the get-go, and how far can you keep going like that? I just kept thinking, it would have been great, because it hasn’t been done in a long time, it hasn’t been done that many times.”

“But that’s the beauty of the races, the competition,” said Santos. “It’s very difficult to win; the percentage speaks for itself. Everybody is against the favorite. You can be the winner by a nose or the loser by a nose. Huge difference.”

Another Hall of Fame retiree, 43-year-old Gary Stevens, calls the 1997 running of the Belmont Stakes one of his most difficult experiences from which to recover. Aboard the Bob Baffert-trained Silver Charm, he lost by three-quarters of a length to Touch Gold, ridden by Chris McCarron.

“I’ve never recovered from Silver Charm, I really haven’t,” he said. “I’ve been told, ‘Oh, you rode him perfectly, blah, blah, blah.’ But I’ve always second-guessed the ride I gave him that day. If I’d done things differently, would the end have been different? It’s something I’ll have to live with. I went from knowing I was going to win the Triple Crown at the sixteenth pole to knowing I was going to lose it 50 yards before the wire. Talk about the highest of highs and the lowest of lows – try knowing you’re going to get it and then seeing a shadow out of the corner of your eye and then it’s over and you’ve lost it.”

McCarron, 53, had missed a Triple Crown score himself with a self-described “screw up,” when he rode Dorothy and Pamela Scharbauer’s Alysheba to a poorly-planned fourth-place finish for trainer Jack Van Berg in the 1987 Belmont.

“It feels greedy to describe it as the lowest feeling you can possibly have, especially considering what you’ve accomplished up to that point,” McCarron said. “But put it this way; I start out at ground level and win the Derby, so I’m at 10,000 feet. I win the Preakness, and I’m at 20,000 feet. Now I’m going to the Belmont and I’m looking at Mount Everest – I’ll have scaled the highest mountain in the world if I win. But I don’t. And all of the sudden I’m right back to ground zero, square one, so I have to swallow it all and convince myself that, you know what, it’s part of the game. In horse racing, you win some and lose a lot.”

The pressure of losing such a bid is heavy, and the circumstances can be overwhelmingly damning for a rider who feels the pressure of this industry’s yearning for a Triple Crown winner.

“It starts to build up when you go into the Derby,” Elliott said. “I guess I got used to it a little bit – it never really goes away after that – but things happen so fast. You win the Derby and now, bam! You’re going to try to win the Preakness. And you win the Preakness and bam! It’s there again going into the Belmont.”

“It’s an exciting time, but mentally draining,” Stevens said. “That doesn’t come so much from the attention, but from feeling responsible to the sport.”

Following a 1999 Triple Crown bid, lost when Bob and Beverly Lewis’ Charismatic broke down in the Belmont stretch, the late Chris Antley left the scene brokenhearted – and those who knew him best believe that feeling contributed to the jockey’s tragic death the next year.

“I honestly think in hindsight that he carried a lot of weight on his shoulders, not only for the horse and the Lewis family and (trainer D. Wayne) Lukas, but for the whole industry,” said Ron Anderson, Antley’s former agent. “He was trying get the Triple Crown this sport needed.”

“After that, I saw the turn and I made comments to family,” said Stevens, who was a close friend of Antley’s. “I told them, ‘I don’t know whether he’ll make it through this deal, because I know what it did to me.’ It tore me up.”

Antley, known for his compassion and sensitivity – but also for bipolar disorder and a history of substance abuse issues – took the Belmont loss like a crushing blow.

“He was very shaken,” said Anderson. “Not only by the horse getting hurt, but by fact that he thought he had a responsibility to win for the sport. I haven’t talked to many people about that aspect, but I think it affected him a lot.”

“The most difficult part in the aftermath is the huge letdown,” said McCarron. “Before that, the time flies by and it seems like the races are right on top of each other. You win the Derby and Preakness and you’re being pulled in every possible direction. You have so many people saying ‘You’re gonna get it, you’re gonna win the Triple Crown, he won the Preakness so easy, you can’t miss…’ The emotional aspect is overwhelming.”

Desormeaux, 38, has already experienced that rush and subsequent letdown. Aboard Mike Pegram’s Real Quiet in 1998, he lost the Belmont in the last jump. He also second-guessed in the aftermath, wondering if he made his move too soon. But trainer Bob Baffert would have none of it, telling his rider to remember the positive build-up and not look back.

“I got a great text message from Kent this morning,” said Stevens. “He said, ‘I’m headed to the Nassau County OTB to help sell our sport.’ But even while he’s doing that, making all the public appearances and conducting all the interviews, he’ll be thinking ‘I can’t screw this up.’ He’s reading what the naysayers are writing and listening to what his own camp is saying; he’s putting every possible scenario in his head, thinking of everything that could happen. I can tell you one thing; he doesn’t want to be the reason this horse gets beat.”

Win, lose, or draw, most of the riders who have come so close to greatness agree on one thing – the sweetness of the journey and the chance of a lifetime is worth the pain of the often-suffered loss.

“Going to the Triple Crown after winning the Kentucky Derby and Preakness is a beautiful ride,” said Santos.

And Elliott summed it up best, with the optimistic attitude of one whose career reached heights he could only dream of.

“You know, ‘Smarty’ was the best horse I’d ever ridden,” he said. “I said at one point, ‘If I could win the Arkansas Derby on this horse, I’d be happy.’ Then we went to the Kentucky Derby, and sure, I was on the best horse, but the best horse doesn’t have to win. When we went on to win the Preakness and it looked like we had a great chance to win the Triple Crown but it didn’t happen, sure, that was disappointing. But you have to realize what a great run I had. I won the Kentucky Derby. I won the Preakness. And nobody can ever take that away from me.’”